Methanol → HCID 178507518, compound

HRID 1819419Notes

Reaction equation

HRID 1819419 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[NH2:40])[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].CO>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[S:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[NH2:40])[N:17]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57885753HCID 57885753, compound

Product 1

HCID 178507518HCID 178507518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above [4-({2-[2-(2-amino-phenylsulfanyl)-benzylamino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (35 mg, 0.06 mmol) in CH2Cl2 (10 mL) was added TFA (1.2 mL). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then treated with saturated NaHCO3. During the work-up, some MeOH was added to solubilize the product in the organic phase. The organic phase was then dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 10:1:0.1 CH2Cl2:MeOH:NH4OH as an eluent to afford 20 mg 70%) of the title compound as an off-white solid, m/z 477.9 (M−1)+.

Workup

  1. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-766ff3699c224e2bbe65f318ce34f867
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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